Enantioselective and Diastereoselective C–H Alkylation of Benzamides: Synergized Axial and Central Chirality via a Single Stereodetermining Step
Jinlei Wang, Haohua Chen, Lingheng Kong, Fen Wang, Yu Lan, Xingwei Li
Abstract
In this report, distally disposed axial and central chirality has been installed in a synergistic fashion via rhodium-catalyzed C–H alkylation of benzamides using N-arylmaleimide as the alkylating reagent, in which the enantio- and diastereo-determining steps are merged into a single one. The coupling system features mild reaction conditions, broad substrate scope, and excellent enantio- and diastereoselectivity. The chiral induction has been enabled by judicious choice of a chiral rhodium cyclopentadienyl catalyst that serves to control both the orientation of the olefin unit and the prochiral C–N bond.
Topics & Concepts
Enantioselective synthesisRhodiumAlkylationChirality (physics)Cyclopentadienyl complexCatalysisChemistryAxial chiralityOlefin fiberReagentCombinatorial chemistryStereochemistryAsymmetric inductionOrganic chemistryPhysicsQuarkChiral symmetry breakingNambu–Jona-Lasinio modelQuantum mechanicsCatalytic C–H Functionalization MethodsAxial and Atropisomeric Chirality SynthesisSynthesis and Catalytic Reactions